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Methyl Cinnamate → Methyl 4-methylene-2-phenylcyclopentanecarboxylate, trans-
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Methyl Cinnamate | HCID 637520 | — |
| 反応物 | 2-(Trimethylsilylmethyl)allyl acetate | HCID 4428347 | — |
| 触媒 | 1,2-Bis(diphenylphosphino)ethane | HCID 74267 | — |
| 触媒 | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | Methyl 4-methylene-2-phenylcyclopentanecarboxylate, trans- | HCID 12537224 | 92.5% |
反応手順
A mixture of methyl trans-cinnamate (5.0 g, 31 mmol), tetrakis(triphenylphosphine) palladium(0) (2.6 g, 2.3 mmol), 1,2-bis(diphenylphosphino)ethane (0.70 g, 1.8 mmol) and 2-((trimethylsilyl)methyl)-2-propen-1-yl acetate (6.90 g, 37 mmol) in THF (60 mL) under argon was heated to reflux for 4 h. An additional aliquot of 2-((trimethylsilyl)methyl)-2-propen-1-yl acetate (3.40 g) was added and the reaction was continued for another 16 h. The volatiles were then removed in vacuo and the residue was purified by FC (10% ethyl acetate in hexanes) to afford the title compound (6.2 g).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06472410B1 |
| 出典データセット | uspto-grants-2002_10 |
| ORD ID | ord-79e976a22e304948b843938dd12dbcf3 |
| 出典メモ | uspto-grants-2002_10 |